Diethyl Ether → HCID 178497985, compound

HRID 16748Notes

Reaction equation

HRID 16748 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]2[CH:12]=[C:13]([NH:16][C:17]([C:19]3[CH:20]=[CH:21][C:22]([C:25]([OH:27])=[O:26])=[N:23][CH:24]=3)=[O:18])[NH:14][N:15]=2)[CH:6]=[CH:7][CH:8]=1.S(Cl)(Cl)=O.[CH2:32](OCC)C>CO.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]2[CH:12]=[C:13]([NH:16][C:17]([C:19]3[CH:20]=[CH:21][C:22]([C:25]([O:27][CH3:32])=[O:26])=[N:23][CH:24]=3)=[O:18])[NH:14][N:15]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 178490047HCID 178490047, compound

Product 1

HCID 178497985HCID 178497985, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred suspension of 5-[[5-[2-(3-methoxyphenyl)ethyl]-2H-pyrazol-3-yl]carbamoyl]pyridine-2-carboxylic acid (55 mg, 0.15 mmol, 1 eq) in methanol (0.5 mL) was added thionyl chloride (23 uL, 0.32 mmol, 2.1 eq) dropwise. The resulting solution was heated at 50° C. for 3 h. The mixture was concentrated in vacuo to yield an orange solid. This was dissolved in DCM and washed with saturated aqueous sodium hydrogen carbonate and brine. The organic layers were dried over magnesium sulphate, filtered and concentrated to give the crude product as a yellow solid. Trituration with diethyl ether gave the title compound as a white solid 27 mg (47%); 1H NMR (400.13 MHz, DMSO) δ 2.92 (4H, s), 3.74 (3H, s), 3.92 (3H, s), 6.49 (1H, s), 6.25 (1H, m), 6.82 (2H, m), 7.19 (1H, t), 8.14 (1H, d), 8.46 (1H, m), 9.20 (1H, d), 11.11 (1H, s), 12.25 (1H, s) MS m/z 381 (MH+)

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto yield an orange solid
  3. washwashed with saturated aqueous sodium hydrogen carbonate and brine
  4. dry with materialThe organic layers were dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product as a yellow solid

Sources & evidence

ORD record
ord-0135c9fea0a64d1daa4f640e9881d6da
Source dataset
uspto-grants-2010_06
Patent number
US07737149B2

Reaction notes

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